Issue 37, 2020
From the journal:

Chemical Communications

Ring-opening iodination and bromination of unstrained cycloalkanols through β-scission of alkoxy radicals†

Jiang-Ling Shi,a   Yuankai Wang,a   Zixuan Wang,a   Bowen Doua  and  Jianbo Wang ORCID logo *a  

* Corresponding authors

a Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China
E-mail: wangjb@pku.edu.cn

Abstract

Ring-opening iodination or bromination of unstrained cycloalkanols with NaI or NaBr and PhI(OAc)2 under visible light irradiation is developed. In this protocol the concentration of I2 is modulated through the generation of triiodide (I3−), thus significantly avoiding undesired side reactions. The reaction is under mild conditions and has a wide substrate scope, thus providing a practically useful method for accessing ω-iodo or ω-bromoketones.

Graphical abstract: Ring-opening iodination and bromination of unstrained cycloalkanols through β-scission of alkoxy radicals

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Article information

DOI
https://doi.org/10.1039/D0CC01720E
Article type
Communication
Submitted
05 Mar 2020
Accepted
26 Mar 2020
First published
27 Mar 2020

Chem. Commun., 2020,56, 5002-5005

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Ring-opening iodination and bromination of unstrained cycloalkanols through β-scission of alkoxy radicals

J. Shi, Y. Wang, Z. Wang, B. Dou and J. Wang, Chem. Commun., 2020, 56, 5002 DOI: 10.1039/D0CC01720E

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